Patent GB-1413491-A (GB)
Title: 3-substituted-2,2-dimethyl-cyclopropane carboxylic acid esters  their preparation and their use in pesticidal compositions
IPC: C07C47/575
Filed: 1973-04-30
Abstract: 1413491 3 - Substituted - 2,2 - dimethylcyclopropane carboxylic acid esters; phosphoranes NATIONAL RESEARCH DEVELOPMENT CORP 15 Aug 1973 24809/72 24810/72 38403/73 30838/72 59184/72 20539/73 and 38403/72 Divided out of 1413491 Headings C2C and C2P The invention comprises compounds having the general formula wherein R<SP>1</SP> represents hydrogen or a methyl group; R<SP>2</SP> represents hydrogen or a halogeno or alkyl group; R<SP>3</SP> represents hydrogen or a halogeno, alkyl (which is different to R<SP>2</SP> when R<SP>2</SP> represents an alkyl group) or carboalkoxy group which contains at least 2 carbon atoms in the alkoxy residue when R<SP>2</SP> represents methyl or R<SP>2</SP> and R<SP>3</SP> together with the carbon atom to which they are attached represent a cycloalkylene ring having at least one endocyclic carbon to carbon double bond; with the proviso that (a) R<SP>2</SP> and R<SP>3</SP> each represent hydrogen only when R<SP>1</SP> represents methyl and (b) when R<SP>1</SP> is hydrogen, one of R<SP>2</SP> and R<SP>3</SP> is hydrogen and the other of R<SP>2</SP> and R<SP>3</SP> is alkyl, that alkyl contains at least two carbon atoms; and R represents a group of formula wherein Z represents O, S, CH 2  or CO, Y represents hydrogen or an alkyl, alkenyl or alkynyl group or an aryl or furyl group which is unsubstituted or substituted in the ring by one or more alkyl, alkenyl, alkoxy or halogeno groups, R<SP>7</SP> and R<SP>8</SP>, which may be the same or different, each represent hydrogen or an alkyl, or alkenyl group, R<SP>9</SP> represents hydrogen or a methyl group, R<SP>10</SP> and R<SP>11</SP>, which may be the same or different, each represent hydrogen or an alkyl group, R<SP>12</SP> represents an organic radical having carbon-carbon unsaturation in a position α to the CH 2  group to which R<SP>12</SP> is attached, A/S indicates an aromatic ring or a dihydro or tetrahydro analogue thereof, x1, x<SP>2</SP>, x<SP>3</SP> and x<SP>4</SP>, which may be the same or different, each represent hydrogen, chlorine or a methyl group, Z<SP>3</SP> represents -CH 2 -or-O-or-CO-or-SD represents H, CN or -C#CH, z<SP>1</SP> and z<SP>2</SP>, which may be the same or different, each represent chlorine or a methyl group and each n which may be the same or different is 0, 1, or 2, with the proviso that R does not represent hydrogen (or an acid chloride derivative of the acid) or an ethyl or allethronyl group when R<SP>1</SP> represents hydrogen, R<SP>2</SP> and R<SP>3</SP> each represent chlorine and the compound is racemic. They may be prepared by reacting a compound of the formula with an alcohol or esterifiable derivative thereof of the formula RQ, wherein Q and Q<SP>1</SP> are functional groups which react together to form ester linkages. The compounds of the formula IX may be prepared by reacting a phosphorane of the formula wherein Z<SP>4</SP> is an organic residue which forms a stable triorgano phosphorus oxide, with a carboxyl compound of the formula and the phosphorane X may be prepared by reacting a substituted methyl halide of the formula with a triorgano phosphine of the formula and, if necessary, treating the resulting quaternary phosphorium with base to cause dehydrohalogenation. The compounds of the invention may be used as active ingredients in insecticial compositions.